Sesquiterpene and acetogenin derivatives from the marine red alga Laurencia okamurai

Mar Drugs. 2012 Dec 14;10(12):2817-25. doi: 10.3390/md10122817.

Abstract

In addition to 13 known compounds, four new bisabolane sesquiterpenes, okamurenes A-D (1-4), a new chamigrane derivative, okamurene E (5), and a new C₁₂-acetogenin, okamuragenin (6), were isolated from the marine red alga Laurencia okamurai. The structures of these compounds were determined through detailed spectroscopic analyses. Of these, okamurenes A and B (1 and 2) are the first examples of bromobisabolane sesquiterpenes possessing a phenyl moiety among Laurencia-derived sesquiterpenes, while okamuragenin (6) was the first acetogenin aldehyde possessing a C₁₂-carbon skeleton. Each of the isolated compounds was evaluated for the brine shrimp (Artemia salina) lethal assay and 7-hydroxylaurene displayed potent lethality with LD₅₀ 1.8 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetogenins / chemistry
  • Acetogenins / isolation & purification*
  • Acetogenins / toxicity
  • Animals
  • Artemia / drug effects
  • Laurencia / chemistry*
  • Lethal Dose 50
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / toxicity
  • Spectrum Analysis

Substances

  • Acetogenins
  • Sesquiterpenes